Vertex Normals Not Facing Correct Directions
Credits to Rahul Chaudhary on https://developer.blender.org/ for the solution.
Turns out the issue is a result of the abnormal scaling I had originally placed on the object to scale a cylinder down to the approximate diameter and height (.078 in XY, 4.888 in Z). Applying the scale immediately fixed the issue.
To clarify, this would be the mesh Blender used to calculate all of the normals, after which it rescaled the mesh to look like the cylinder I had.

Before Applying Scale:

After Applying Scale: